Tails takes Cool Lessons
by Mindl3ss-Cr3ator
Summary: What happens when our little fox friend starts having the urge to be cool like his big figure Sonic? Better question, what happens when Scourge teaches him and his friends find out? By the end, will Tails be transformed forever?; or will he stay himself?
1. Chapter 1

**A/N: This is for NightRider94! This is originally his idea but since he was too busy to write down his great ideas into stories, he posted his ideas on his profile. I came across this one, I messaged him and here it is! Would of been up sooner if I hadn't gotten myself grounded -3-. Oh well, enjoy!**

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In the midst of his friends and fellow Mobians stood none other than Sonic the Hedgehog, victorious yet again. Tails once again had been excluded by the crowd, laying face first in the grass. The young kitsune got up and looked back at the crowd behind him. The group of Mobians had lifted Sonic high in the air like he had just won first place in the Olympics and started to march away; the whoops, cheers and whistles fading away. Tails got up and dusted himself. He watched as the crowd disappeared and sighed to himself.

"Man. Left out again?" Tails sighed to himself again and started to walk away. "Well, I guess I should head back home."

On his walk back home, he kept wondering to himself 'Why can't I be cool like Sonic? Why am I pushed aside like some old computer?' Tails closed his eyes and continued to walk straight again. Suddenly, he bumped into something. In this case, a some _one_. The twin-tailed fox looked up, his ears folding on top of his head as he realized who he had bumped into.

"Uh, s-sorry Shadow! It was an accident, I swear!" The ebony hedgehog stared him down with his cold, ruby red eyes. Tails gulped and took a step back. Before he walked away, his ears shot up as he got an idea. He stayed in the same spot and smiled.

"Hey, Shadow. You're cool, right?"

"What does this have to do with the fact of you just bumping into me?"

"Can you teach me how to be cool?" Shadow scoffed and started to walk away.

"You're on your own kid. I don't need to waste my time trying to increase your self-esteem" With that, the ebony hedgehog strode off. Tails slumped his shoulders and sighed, continuing his way down the street.

Soon, the young fox finds himself walking in downtown Mobius by many clubs, bars and alleys. One place in particular caught his eye. As he passed The Nightingale, he noticed a red echidna sitting on a booth, sipping on his drink. Tails stood outside, thinking whether or not he should go in. Finally he saw no harm and went inside. A few people turned to look at the door but soon turned back to mind their own business; except for one group.

"Seeing what I'm seeing?"

"Yeah but are you thinking what I think you're thinking?"

"He." A malicious smile came across the leopards' mouth. He looked at his friends who smiled in response. They all took one last sip from their glasses and left the club. By the time, Tails was explaining his problem to his friend. The echidna scoffed and took another sip, finishing off his drink.

"Tails, why do you want to be cool?"

"Because I'm so tired of being known as that fox kid and being left out of everything. I was pushed out of the crowd earlier!"

"Bud. I think you're fine just the way you are. You don't need to- hey! Where'd he go?" The red echidna looked around but couldn't see him. He sighed heavily and asked for another drink. Tails on the other hand, had already been on his way home. He looked up. The sky was pretty dark for only seven at night. Suddenly the young fox was yanked into a dark alley. He tried to scream but a piece of cloth was being tied around his muzzle. He was thrown to the hard brick wall, making the young kitsune yelp in response. He opened his eyes a crack to meet a pair of bright green ones. The person in front of him and the group around him started to smile.

Two animals he couldn't make out in the dim lighting closed in on him. One of the two started to kick his gut repeatedly while the other kept punching him. Tails kept yelping and screaming in pain as a response. Tails started to caught out a crimson liquid, staining the concrete with spots and splatters of red. Suddenly, the two stepped away an the third one stepped up. Tails could easily make out this one, he was a leopard; one of the only ones in town. The leopard smiled and held out his hand.

"Pass me the bat." Tails' eyes widened in fear as one of the shadows passed the green eyed one a thick wood bat. The leopard played with the bat in his hands, finding the perfect grip and position. The leopard took the first swing, hitting the twin tailed fox in his side. He screamed in pain, falling to the ground and gripping his side. Tails looked up to see the leopard about to take a second hit. He closed his eyes tightly, waiting for the pain to be inflicted.

"Tails!" The blue blur stood on defense at the opening of the alley way. He bared his teeth, noticing a bat poking out of the shadows. Taking a blind hit, the hedgehog jumped up and started to spin rapidly. He quickly darted straight ahead, hitting all three and knocking them to a wall. Sonic landed on his two feet, feeling a little more calm that the people that were hurting Tails won't wake up for a while. Quickly, the blue speedster picked up his little brother bridal style into his arms and sped off into the night. On the way, Tails fell in and out of consciousness continuously. Before blacking out, Tails only heard the distressed tone in Sonic's voice, begging for the fox to stay with him.

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**And that's chapter one!**

**Tails: O.O**

**Shadow: Hmph.**

**Knuckles: Am I a drunk? What was I drinking!**

**Whatever you want, I guess.**

**Knuckles: Raspberry lemonade -3-**

**Sonic: Man, this sucks. Are you gonna kill Tails?**

**You'll have to wait and see. R&R and stay tuned!**


	2. Chapter 2

After a long while, I finally got a chance to finish this chapter! Sorry it took so long, I am under punishment until November 11th so progress will be slow. Thank you for being patient and I hope you enjoy the update!

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"How you feeling Tails?"

Tails moans and slowly sits up on his bed, rubbing his sore head. He looks up at the blue blur then at a pale yellow rabbit who had a bowl of soup in her hands. Tails blushed at the sight. He's had a crush on little Cream since the first time he met her but was too shy to do anything about it. Cream set the bowl on the nightstand and flashed the kitsune a warm, loving smile.

"Hi Tails! I'm happy to see you're finally awake."

"Wh-what happened to me?" Sonic's brows furrowed.

"Well... you we're jumped by some goons the other day. You're lucky I came in time or..." Sonic trailed off lost in thought of the possibilities. He shook his head and smiled. "That doesn't matter anymore. At least you're awake!" Tails sat up in bed, giving Sonic and Cream a questioning eyebrow.

"Wait... you said the other day. How long have I been asleep?" Tails looked up at his brother figure with curious baby blue eyes. Sonic bit his bottom lip and gulped. Cream closed her eyes and sighed. Tails tilted his head to the left and sighed. "That long, huh?" Sonic and Cream only nodded their head. Tails sighed and got out of bed.

"Something wrong, buddy?" Tails looked up at Sonic, wondering whether he should bother asking. Finally, he sighed.

"Sonic? Can you teach me how to be cool?" Sonic smiled and ruffled the young fox's fur.

"Buddy. I think you're cool just the way you are! Why do you wanna change?"

"Because... I'm so tired of being left out of everything! I mean, you get all the attention, publicity, rewards, you even get to go to exclusive parties! I just want to be noticed. To be somebody..." Tails looked down and flattened his ears against his head. Sonic kneeled down and placed his hand on his little brother's shoulder.

"Come on bud. How about we spend the day together? Just you and me." Tails looked up.

"Really?"

"Of course", Sonic replied giving Tails a classic smile and thumbs up. The young fox smiled and threw himself against the blue hedgehog's peach chest in a friendly embrace. But the moment was short lived when Vector came into the room with a letter in his hand.

"Yo Sonic, guess what? The president invited you to a fancy lunch thing today at twelve! Cool huh?" Suddenly, Tails felt an unknown rage inside him building up. He pushed Sonic away from him and pushed his way past the confused croc. He ran down the stairs and ran out the door. Sonic groaned and ran down the stairs. When he got to the door, his friend was out of sight. He pounded his fist against the door frame. After a few minutes, Vector comes behind Sonic rubbing the back of his head.

"Yeesh. What's his problem?" Sonic turns to face Vector, fire in his olive green eyes. In a flash, Sonic had Vector in a choke hole.

"You idiot! I'm going to kill you!"

"Make it a slow and painful death", Shadow said. Suddenly, the ebony hedgehog came next to the blue hedgehog holding a rope. "You're going to pay for ransacking my bedroom and stealing my money you green bastard!"

While Vector was being beat up by the two hedgehogs, Tails had stopped at a park to catch his breath. Sitting on the wood bench with the wind blowing through his bangs and the lingering scent of cherry blossoms, he almost started to relax. Almost. Suddenly, he felt a tap on his shoulder. He turned around to face a pair of icy blue eyes. Tails blinked a few times, not believing what he was seeing. A green hedgehog stood before him wearing a black leather jacket with flame designs on the shoulders. He wore red sunglasses that sat proudly on top of his head and two scars on his chest. A toothy smile played on his face. Next to him was a red fox with brown hair. She also had blue eyes, yet they we a darker blue. She wore a black micro mini with matching black knee high boots. She wore a white tank top and an amused smile on her face.

"Well, long time no see kid! Did blue finally kick you out of the team?", Scourge said casually. Fiona smiled and linked arms with the green hedgehog.

"I guess they finally realized how worthless you really were", Fiona added rudely. They both started to laugh. Finally, Tails snapped.

"What do you want!" Fiona raised an eyebrow, Scourge smiled, amused by the young fox's outburst.

"Oh, a little feisty eh?" The green hedgehog propped his elbow and leaned on the bench and closed his eyes as if deep in thought. "Who shoved a stick up your ass?"

"It's none of your business! Why do you care anyways."

"Good point. I don't." Scourge opened his eyes and straightened himself up. Fiona smiled and started to stroke the leather jacket. The green hedgehog gave one last glance to Tails and walked away. "Later kid." Tails stayed in his place, arms crossed and eyes closed. Suddenly, he got another idea he thought was so crazy, it might work. The kitsune got up from his seat and started to follow the two, hoping he wouldn't get killed in the process.

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And there you have it. What is Tails' plan this time? Stay tuned for the next chapter! R&R!


	3. Chapter 3

**Sorry for the long wait. I have been busy with other things but hopefully, I will start to update this story sooner. **

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Scourge and Fiona were at the Nightingale, each drinking a Seabreeze. The fox looked up and let out a long sigh. The green hedgehog turned at her direction, his icy blue eyes cold as the orange fox approached. Scourge turned around in his seat, drink still in hand, and took a long sip. He finally set the glass down next to him and gave him an irritated glare.

"What do ya want now kid?"

"I'm just going to get to the point." Tails took a deep breath."I was in downtown when Sonic had just saved everyone from eggman. I was left as usual so-"Scourge cupped his hand in front of the young kitsunes' muzzle and sighed. He looked at Tails seriously, cocking an eyebrow.

"Start over again. This time say it slower and make it quick, got it?" Tails quickly nodded his head, waiting for the green hedgehog to remove his hand from his muzzle since he was starting to have trouble breathing. He exchanged a look at Fiona before taking his hand away. Tails took a deep breath, taking a few moments to catch his breath. Fiona sighed, impatiently tapping her fingertips against the smooth black counter top.

"Out with it kid!"

"Can you teach me how to be cool!" Tails said, almost gushing the words like an anxious school girl. Scourge and Fiona shared a glance, took a look at Tails then looked at each other again. Finally, the two broke out in a laughing fit. Tails' ears flattened against his head, knowing that somehow this was a bad idea. It wasn't even worth the try. As Tails turned to walk away, Scourge called out "That's right kid, just walk away! You don't belong here anyways!" then turned around in his seat. As the inhabitants in the club started to laugh at him, a nerve inside the orange fox finally snapped. He turned around and marched towards Scourge, who was laughing with his friends about what had just happened. Tails extended his arm and grabbed the collar of Scourge's jacket and yanked it, making the green hedgehog stumble out of the seat. He turned around to see Tails, not knowing who was angrier.

"What the hell's your problem kid!"

"Listen bub! I've been rejected, beat down and made fun of my whole life! If you think you can just try to put me down in front of all these people, you got it all wrong! Not this time!" Tails grabbed the hedgehog by the collar of his jacket again, now eye level to each other. Scourge's eyes widened a little, somehow impressed by Tails' behavior. Suddenly, Tails was grabbed from behind from the forearms, being dragged out of the club. Before the two pit bull guards threw the fox out, they were cut short by slow clapping.

They turned around, seeing that it was Scourge clapping his hands, a toothy grin on his face and a questioning expression in his eyes. Scourge stopped clapping after a while, signaling the guards to let the fox go. Tails was set down then walked over to Scourge who was waving him over. Tails sat in a booth next to Scourge's, now more confused then ever. The green hedgehog sat in his seat and turned to smile, the same smile on his face. Scourge placed his hand on his shoulder, starting to pat in a little roughly.

"You got guts; standing up to me like that. Maybe you aren't such a lost cause after all". As Scourge said this, Tails' could of sworn he saw _pride_ in the hedgehog's blue eyes. Scourge removed his hand off the others shoulder, waving over the bartender. She quickly scurried over, a big smile on her face.

"What can I do for ya Scourgey?" Fiona growled under her breath. Scourge smiled and winked at the bartender when Fiona wasn't looking. She nodded understanding and smiled, looking at the three in front of her. Scourge went through his pockets and pulled out a crisp ten dollar bill. He slid it to the bar tender and smiled.

"Ten whiskey shots." The bartender took the bill and walked away. A few moments of silence went by, the only sounds were the clinking of glass, the game of pool in the back of the club and drunks fooling around. Finally, the bartender came back with ten shot glasses and the bottle of whiskey, setting it on the table. She poured the drink equally into the glasses then walked away. Scourge and Fiona took one of the small glasses into their hands and drank it a couple of gulps. They both set the glass down, sighing in content after wards. The green hedgehog smiled as he slid one of the shots I front of Tails. The young fox's eyes widened a bit, realizing what Scourge wanted him to do. He looked at the drink.

"I can't drink this. It's alcohol"

"Live a little! You wouldn't want to disappoint me now, would you?" Scourge glared the fox down, the small smile still on his face. Tails kept his eyes on the drink for a while, wondering if he should do this or not. Fiona sighed.

"He's a waste of our time. He's too good to do anything like this!" Scourge turned around to tell the red fox to shut up until they heard a clank against the table. They both looked at Tails who was now taking another shot. Scourge smiled toothily, a mischievous tint in his eyes as he watched the fox drink shot after shot. Finally, the last glass clanked against the table, the young fox panting a little. Scourge turned to Fiona with an 'I told ya' look. Fiona only forced a smirk and walked out of the club. Scourge turned to Tails, an impressed look on his face.

"So buddy. You think you want another shot?" Tails peered up at the green hedgehog, his baby blue eyes brightening. Tails smiled.

"Why not? Let's do it!" Scourge turned and raised his hand, a big mischievous toothy grin on his face.

"Oh waiter!" he singsonged.

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**End of chapter 3! What happens to Tails? What is scourge planning? What will his friends do when they find out our cute fox friend is hanging out with all the wrong people? Your questions will be answered by the end of this story! **

***I'll try to update this story at least once or twice a week so keep an eye out for any updates!**

**Hope you enjoyed this update! R&R and stay tuned!**

**Peace!**


	4. Chapter 4

Knuckles and Sonic were at home, waiting for their fox friend to arrive. It was very late at night and he's been gone the whole day. Sonic paced worriedly up and down the living room. Knuckles was sitting in a chair by the window eating an apple. Every once and a while, the red echidna would stop eating and peek out the window, looking for any sign of the young fox. Looking out that window for the millionth time that day, he let out an irritated sigh and got up from his seat. Sonic's olive green eyes fell upon the echidna as he approached the staircases.

"Where are you going?" Sonic asked. Knuckles sighed again and looked over his shoulder.

"I'm going to bed."

"Now! Tails is still out there, in the cold city with all of these criminals and all you can think about is sleep!"

"It's late and I'm tired. You should get some rest instead of wasting your time on someone who might not even come home tonight" With that, the echidna turned around and made his way up the stairs. Halfway up the stairs, the two suddenly hear a door creak. They whip their heads around to see Tails at the doorway, carrying a brown paper bag in hand. Tails lifted the bag to his mouth, drinking the remainder of the whiskey bottle. Once there wasn't a drop left, the young fox threw it over his shoulders and smiled lazily.

"Hey guysh. What'sh ya up tu?" Tails walked into the room, dragging his feet along the hardwood floors and looking like he would fall over any minute. Sonic and Knuckles could only stare as the young fox settled down on the couch and yawned sleepily. The two exchanged a look and crept upstairs, making sure not to wake the now sleeping fox. As our blue hero was about to enter his room, Knuckles placed his hand on his shoulder. Sonic turned around to see bloodshot amethyst eyes. Sonic yawned.

"Yeah Knucklehead?"

"You know, I'm starting to get worried about Tails. I mean..." Knuckles sighed, not knowing how to explain to Sonic how his friend might be hanging out with all the right people but he couldn't for two reasons. He just couldn't bring it to himself at the time and he was too tired to explain. Plus the red echidna couldn't assume the possibility of him hanging out with drunks and criminals. At least not yet. Knuckles turned around and started to walk away, dragging himself most of the way. "I'll tell you tomorrow" he said sleepily.

Sonic yawned again and turned away into his room. He plopped onto his bed face first and immediately fell asleep.

The next morning, Knuckles and Sonic met outside of Tails room. Surprised, they took a step back and looked at each other.

"What are you doing here?" Sonic asked. The red echidna crossed his arms and closed his eyes.

"Isn't it obvious? You and me are here for the same reason; to check on Tails. What do you think happened to him yesterday?"

"I don't know Knux" Sonic said as he opened the door; "But he hasn't been the same lately." Sonic opened the door without peeking inside. Knuckles only said 'huh?' Confused, the blue blue peeked inside the room and had the same reaction. The room looked the same except one of the valuable piece of the puzzle was missing. Tails.

"Hit me with your best shot!" Scourge said patting his stomach. Tails only cocked an eyebrow, staring at the scared peach tummy. He looked back at the hedgehog.

"Really?"

"Yeah" Tails looked down at the green hedgehog's stomach again.

"In the stomach?"

"Yes in the stomach now punch it already, I'm losing patience and you don't wanna see me angry!" Tails immediately clenched his fist and punched Scourge's belly. The green hedgehog looked at the fox in disbelief. "Kay kid. I know you can punch harder than that. Like this." Scourge turned around and punched Fiona's gut, making her fall to her knees, gripping her stomach. Alarmed, Tails kneeled down to the fox.

"Hey! Are you okay?" The red fox hesitantly looked up at the young kitsune and forced a smile. She staggered to her feet, still wrapping her arms around her stomach.

"Just peachy" she said through gritted teeth. She looked at Scourge with enraged, pained blue eyes. Scourge only turned away from her, starting to walk out of the room. Fiona limped to the couch, sighing in relief as she laid herself on the soft cushions. Tails walked over to her and placed his hand on her stomach.

"Are you sure you're okay?" Tails asked once more. Fiona slowly looked up, a child like expression on her face. Tails gasped, noticing her eyes were becoming glass-like.

"Listen kid. Don't worry, I'm fine. But-" Fiona stopped to make sure the fox was listening. "Please, promise me... don't go too far with this. I mean_ look at me_. I used to be the sweetest girl and I worked with the freedom fighters. Now look at me." She stopped and looked at herself in the mirror, a small smile on her face as she saw her old self in the reflection. A tear ran down her cheek as she closed her eyes and looked at the floor. "All to impress a boy who doesn't even like me back"

Tails eyes widened a little, recalling the good times they had when she was with the freedom fighters. Then Scourge came... Tails looked at the red fox, placing his hand on her cheek. Surprised, she looked up to see the other fox smiling.

"I promise. When it goes too far, I promise you I'll stop" Fiona smiled as the young fox placed a small, friendly kiss on her cheek. A small, barely noticeable blush appeared on his cheeks as he walked into the other room. Scourge was at the table, drinking plain water. The green hedgehog smiled as he got out of his seat and pulled on his leather jacket. Confused, Tails walked over to the hedgehog and tapped his shoulder. Scourge turned around and placed his arm around Tails shoulder.

"C'mon kid! We're gonna hit the town!"


	5. Chapter 5

See? What did I tell ya? When I make a promise, I tend to keep it

Well, I hope you enjoy this update!

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In downtown Mobius, Scourge had taken Tails to one of his favorite stores. Different leather jackets of every shape and size hung along the walls and racks. On a display rack there were a lot of unique sunglasses, all different colors. The back was loaded with row upon rows of gloves, shoes and other accessories. Scourge patted his back, a small smile on his muzzle.

"This is your next mission. Pick out a jacket and new shoes. You can get somethin' else if ya want. When you're done, you know where to find me"

"By the sunglasses?"

"You're catchin' on fast pal" The green hedgehog gave him a wink and started to walk away. Scourge's choice of words and his attitude sent chills down his spine. That sounded something like Sonic had said to Knuckles before a long time ago. _Maybe the two hedgehogs _do_ have something in common_. Tails shook his head, losing the thought only to come across another. _I wonder how Sonic is doing_.

"We gotta keep looking! He has to be around here somewhere!" Sonic went inside the Nightingale, hoping maybe he would find his two tailed friend with someone he knew. _Like say, I don't know,_ Vector? Sonic thought to himself. Seeing his little brother with anyone of his friends would reassure his safety. At the moment, he could care less if he was with a drunk. He sat down at a booth and sighed. A bartender came up to him with a big smile on her face.

"Can I get ya anything, hun?" Sonic looked up at the female and sighed, placing a five dollar bill on the table.

"Give me a Tequila Sunrise" She smiled and turned around. She set a tall glass in front of Sonic and turned around, starting to pour the ingredients into the blender. The whirring lasted for a few moments before coming to an abrupt stop. The woman turned to Sonic, the same smile still on her face. As she started to pour the drink into his cup, she couldn't help but feel sorry for the hero. After Sonic took the drink and thanked her morbidly, she came from behind the counter and sat in the seat next to him. She sighed, staring at him worriedly.

"What's wrong? You seem so down." Sonic took a small drink from the smooth orange liquid, letting it satisfy his thirst. He looked at the bartender in the eyes.

"My friend. He's been acting different. Last night he came home at two in the morning and this morning I went to check on him and he was gone. I just don't know what's gotten into him"

"You're worried about him and trying to find him, right?"

"Yeah. I mean, he's like a little brother to me. We're close and all but... I never felt this far apart from him. I just wanna help" Understanding, she nodded her head.

"How does your friend look like? I might of seen him round'. Never know" Sonic took out the picture out of his white fleece jacket and handed it to the stranger. She gently took it from his hand and unfolded it. After a minute, she set the picture on the table and set it down. Sonic looked down to see her pointing at Tails' face.

"I've seen him before"

"Really?" Sonic almost yelled. He was excited to finally talk to someone who might know where he is. He blue hedgehog's tail wagged quickly behind him as he finished off his drink. She nodded her head, passing the photo back to the hedgehog. He quickly stuffed it in his pocket and immediately turned his overjoyed olive green eyes.

"Yeah. He was here yesterday; drank a few whiskey shots" Sonic's ears shot straight up and his tail stopped wagging. His eyes were hollow as he stared at the woman. "What?" he whispered.

"Yeah. He was here with a red fox and a green hedgehog that looked just like you" Sonic couldn't believe what he was hearing. Scourge is in town! Sonic shot out of his seat, shaking the woman's hands to thank her then running out of the door. She blinked her eyes a few times then sighed, looking down at her apron.

"What a strange guy"

The young kitsune looked around, feeling out of place. Every time he went down a aisle, there would be an unkempt stranger staring at him with piercing death glares and mocking smiles. Tails gulped and continued down the aisles, looking for something he would actually wear. Finally, he came across a row of leather jackets his size. He slowly paced up and down the empty aisle until he finally saw it. On a single hanger for display was a black leather jacket, the back embroidered with a big letter T in flames. He took it off the hanger, gave it one last look and shrugged his shoulders. He pulled the jacket on and walked in front of the body length mirror. Tails popped the collar and turned around, smiling as he looked at himself.

"Nice pick" a voice said behind him. The fox turned around to meet a pair of deep blue eyes. He smiled as he hugged the red fox.

"Thanks! What are you doing here?" Fiona looked at the orange fox and smiled winking at him.

"I felt a little better and decided to drop by to buy some new boots. I'm guessing clothes make the fox?" Tails looked down at himself, his smile widening. He looked back up at the fox.

"I guess. It was Scourge's idea"

"I can tell" She looked around the store and sighed to herself. She looked back at Tails. "Where is that bastard"

"Looking at sunglasses. He told me to meet him there when I was done." Fiona nodded her head, closing her eyes. For a while, there was a long moment of silence between the two. Tails placed the jacket back on the hanger and draped it on his arm. He turned to look at Fiona, a small smile on his face. "Hey Fi. Do you think you can help me pick out some shoes?" The red fox whipped her head to the side, her bangs sweeping to the side.

"Sure. It's not like I got anything better to do" she replied smiling. Tails smiled back at her, the two making their way to the shoes. When they arrived, the first thing he noticed was that most of the shoes had straps with metal studs or buckles, even both. He shivered as he put down half of the shoes in the aisles. Fiona smiled, walking past him and advancing to the end. She kneeled down, looking up at the approaching fox.

"What's your shoe size?"

"Uh... six and a half" he replied as he set the jacket down on the bench beside him. He sighed, happy he got the warm jacket off him. He was starting to get hot. Fiona turned back to the shoe boxes, looking for his size. Finally, she pulled out a gray box, setting it on the carpet. She flipped the lid open and took out a sneaker. It was all black with the exception of the red graffiti design on the side that read 'hot'. She held it up proudly like she had just won the Nobel Prize.

"You like?"

"Yeah" Tails replied, taking the sneaker out of her hands. He turned it around, admiring the design. Fiona smiled, standing up with the shoebox in her hands and taking her place next to Tails. He turned to Fiona, placing the shoe in it's rightful place. The red fox placed the box in his arms and smiled.

"Thanks for the help" Tails said. Fiona smiled and said a simple 'you're welcome'. Before she turned to walk away, she leaned closer to Tails and gave him a kiss on the lips. The kitsune blushed as Fiona walked away looking over her shoulder, waving at him. Tails only stared back blankly, waving back slowly. She giggled and turned around, walking out of the store. After a while, he snapped out of his daze and started to walk towards Scourge. When he met up with him, the hedgehog was picking between two sunglasses, He looked at Tails, a smile on his face and a pair of sunglasses in each hand.

"Which one should I get. Red with black shades or black with red shades?" Without looking, the young fox simply pointed to the red shades. Scourge placed the black ones back on the rack, a toothy grin on his face. "Red with black it is! C'mon bud. Let's pay and get outta here. There's still a lot more stuff we need to get done before tonight!"

"Yeah" Tails expressionlessly. As he followed Scourge to the registers, he couldn't help but stop thinking about that kiss Fiona had just given him. _Is it true that maybe, just maybe, she really did like me back then? Is it possible that she might still like me?_

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And finished!

What is Scourge going to make Tails do next? We'll, you'll find out soon enough!

R&R, stay tuned and hoped you enjoyed!


	6. Chapter 6

**I know, it's been a while. But hey I'm back with a long chapter and that's all that matters most, right?**

**Tails: Oh no. Not again!**

**The public is enjoying this story. Right!**

***applause***

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"Chug! Chug! Chug! Chug! Chug!" Tails sighed heavily and slammed the glass mug on the counter, wiping his muzzle as the crowd around him started to cheer and clap. He got a pat on the shoulder from Scourge before he turned and walked away. Tails panted slowly as the crowd around him started to disperse, returning to their own business. The bartender, who he now knew as Wendy, leaned over the counter, giving him a wink.

"That was some serious chuggin'! I bet you must be getting pretty dizzy" The kitsune shook his head slowly, staring at the orange mongoose in her green eyes.

"No... but there's something I wanna give you." Tails leaned over the counter, placing a long kiss on her lips. For a few moments, she stayed in place, returning the kiss with a giggle in between breaths. When they pulled away, Tails winked walking away. After playing a few rounds of Pool and having a few more drinks, he found the green hedgehog at a table, smoking on a cigarette. By the time Tails got there, Scourge had just about finished smoking the whole thing. He exhaled a puff of smoke to the side, then smiled. He looked at the fox.

"Well buddy. I gotta admit, you know how ta live!" Scourge threw the cigarette on the tile surface of the floor, stomping it out with his big shoe. Just then another bartender came by, a lavender cat with light blue, almost white, hair that fell over her shoulders. She set a couple of mugs on the table and winked at the two, Scourge only giving her a wink back as a response. The green hedgehog slid a mug at Tails, lifting his in the air. "To the new and improved Tails!"

"To the new and improved Tails" the fox repeated. Just as the two lifted the mug to their mouths and took a long, hearty sip, the club doors burst open. In an instant, a blue hedgehog stood by the fox's side, eyes wide.

"Tails! What are you doing!" As Sonic extended his hand to grab the drink from his little brother, Tails pulled it away from him, giving him a cold stare. Sonic nearly froze, shocked to see the coldness of his baby blue eyes. Knuckles walked next to the blue hedgehog, giving Tails a confused stare.

"C'mon bud. We're going home. _Now_!" The echidna shot out his hand to grab Tails only to be grabbed by the wrists. He growled as one of the guards placed his hands tightly behind his back, making it nearly impossible to move. Sonic only yelled out 'Hey!' as another guard did the same. Tails stood up, staring eye to eye with the enraged echidna then looking at the blue counterpart.

"Listen; both of you. I don't _care_ what you want anymore. What _I_ want is to stay with Scourge. And guess what; I'm not coming home neither. Consider your time wasted." He snapped his fingers and turned his back towards them. "Take them away boys. And make sure they don't get back in" With that, the fox could only listened as the two protested, their shoes dragging along the welcome mat. Before long, Tails couldn't hear their voices anymore and 'hmphed'. Satisfied, he sat back in his seat and took a quick sip from his mug as the crowd around him started to cheer once again. Tails and Scourged raised their mugs once again, laughing before taking a long sip.

By this point, Scourge had left with some friends for the night, claiming the fun here was over. Tails was one of the only people left in the nearly deserted club, sipping on some water to settle his churning stomach. As he took another sip, Wendy came back on the stage as a drunk dog walked off. She clapped and cheered as he fainted.

"Let's hear it for the drunk dog! You've heard 'Like a Virgin', "Love like This' and 'You got it bad'. But now, get ready for a little R&B song. Everyone, give it up for Fiona Fox with 'So hard'! The young kitsunes ears shot up as he peered up. Sure enough, walking on the stage was Fiona. She wore a short black dress and strappy black heels that clacked with every step. Her hair was worn loose over her shoulders, only gloss for make up. Some people in the crowd wolf whistled as she sat on the piano, holding the microphone in her hand. She gave a small smile and closed her eyes as the song started, waiting for the perfect time to jump into the beat. Tails got up from his seat, taking a seat at the table in front of the stage. She took in a deep breath as she tilted her head back.

_He made it so hard to trust someone  
__He made it so hard to fall in love_

_I'm not trying to mess up this relationship, thinking  
__'Cuz the last man did me that way, you're gonna do the same things'  
__I don't wanna be this way, hoping you can change  
__The way that I feel_

_You see I trusted him with everything  
__Never held back anything  
__Thought we'd be together for the rest of our lives  
__So suddenly he took his love away  
__And it made it hard to trust again_

_I know I've been holding back but he really hurt me bad  
__I don't wanna take my past and put it all on you  
__I'm not tryin' to hold you back, really hope you understand  
__I don't know what I'm gonna do_

She opened her eyes, now glass-like. Maybe it was just the lighting the fox thought to himself. Fiona directed her gaze at him, pain visible in her blue eyes again. Tails felt a sharp pang in his chest.

_When I think of what he did to me, makes it hard to fall in love  
__When I think about just what I need, makes it hard to trust someone  
__Baby I gotta let go, don't wanna miss out on love this time  
__Gotta leave those things behind_

She laid down on the grand piano, staring into the audience as she continued to sing. She usually laid on her back when singing this song, not because it was comfortable. Because it prevented the tears from cascading down her cheeks.

_Whatever's yours you call it ours, send flowers  
__With love you kept me showered, but so did my ex-man at first  
__You see what started out so simple, all flew out the window  
__There I go comparing you to him again_

_It keeps holding me down, I gotta let it go  
__I wanna give love a chance cuz' you may never know  
__Baby you could be the one for me, yes the only one for me  
__And I don't wanna lose a good thing, no_

_I know I've been holding back but he really hurt me bad  
__I don't wanna take my past and put it all on you  
__I'm not tryin' to hold you back, really hope you understand  
__I don't know what I'm gonna do_

_When I think of what he did to me, makes it hard to fall in love  
__When I think about just what I need, makes it hard to trust someone  
__Baby I gotta let go, don't wanna miss out on love this time  
__Gotta leave those things behind_

Fiona sat up on the piano again, her leg dangling off the side. Tails only stared in amazement. He never knew she could_ sing._

_One disappointment, one heartbreak  
__Too many mistakes in love I've made  
__I can't come with all this baggage thinkin' he's gonna have it  
__See I know I'm being selfish but I gotta let it go_

_Close that chapter, close that book  
__Faith in love is all it ever took  
__That's why I never gave up and never gave in  
__Cuz' I know true love is waitin' for me again_

She sure knows how to sing a high note. And hold it.

_I know I've been holding back but he really hurt me bad  
__I don't wanna take my past and put it all on you  
__I'm not tryin' to hold you back, really hope you understand  
__I don't know what I'm gonna do_

_When I think of what he did to me, makes it hard to fall in love  
__When I think about just what I need, makes it hard to trust someone  
__Baby I gotta let go, don't wanna miss out on love this time  
__Gotta leave those things behind_

_He made it so hard to trust someone  
__He made it so hard to fall in love_

As the song ended, the young fox could of sworn seeing her wipe a tear from her eye as she left the stage. The orange mongoose got up again, starting to talk and see if anyone would offer to sing before singing herself. Tails watched as Fiona pulled a trench coat and left the club silently. Somehow finding himself worries, the orange fox got up from his seat, following Fiona out the door. He didn't get as far as he thought he would. Instead, he found himself at the park, looking for the red fox.

After walking around the park a few times, he finally spotted a figure on the bridge, looking down at the running stream beneath. Tails walked closer to her, picking up the pace as he realized the swaying skirt of a black dress and the red trench coat. As he heard her sniffle and saw her wipe a tear away, Tails placed a hand on her shoulder. She jumped and turned around, sighing in relief seeing the familiar fox.

"Oh. Hey Tails" she replied.

"Hey. Um, I saw you singing at the club. You know..."

"Right" she replied slowly. "There's actually a reason I sang that song" Fiona looked down at her reflection in the stream, watching a tear trickle to the bottom. Tails bit his lip as he hugged her with his free arm, the other in his pocket. She swallowed a sob and bit her bottom lip for a while, stretching the silence between them. Finally she closed her eyes, her head still in the direction of the running water.

"I feel it's unfair to you. I mean, you've done so much for me but I haven't really done anything in our relationship to prove it"

"Fi, it's o-"

"No, it's not okay" she replied cutting in, her eyes now wide open. " I want to do more but it's just... so hard. You wanna know why we broke up?" Tails slowly nodded his head, pressing her closer to him. Fiona shakily sighed.

"I gave Scourge everything and he did the same for me. For a while. Suddenly, he started flirting with other girls, staying out with his friends, going to more parties. One day he came home, apologizing to me and saying he would make it up to me. I was still angry at him and told him to leave... then that night..." She trailed off, looking up at the sky. She looked down again, a single tear running down her cheek. The red fox looked back up at Tails, a glint of anger in her eyes. " And you know what happened? He raped me!" she yelled. She suddenly hung her head, starting to sob. "Chaos, I felt so helpless. It's like no matter what I did, it only gave him another idea or advantage. He put me through hell that night!"

As her salty tears trickled into the stream, Tails couldn't help but to feel sorry for Fiona as he wrapped his arms around her. Fiona peered into the stream below her, another tear falling into the water as she looked at the reflection once more. She felt safe with the orange fox around. The arms holding her weren't threatening, they were loving. Understanding. Friendly...

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**Finished! Tell me what you think. R&R, stay tuned and hoped you enjoyed :D**

**Tails: Help me. Please.**

**Silence!**

**The song used was 'So Hard' by Ciara**


	7. Chapter 7

**I bet you all forgot about this story huh? I'm soooo sorry I haven't been able to update. There was the author's block and computer time limits and punishments! *sigh* Well, at least I got the time to finish this chapter today. Read on.**

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It's been weeks since Tails' had left Sonic and the gang. Deep inside, he really missed them. There were times he wanted to sneak out and just beg the gang for his old life back. But it wasn't that easy. They probably wouldn't even let him near the place. The kitsune sighed as he closed his eyes, memories and images from his past flashing through his head. How he missed those days.

"TAAAAAILS!" Snapping out of his thoughts, the kitsune screamed and fell out of his seat. He collided to the floor. He looked up to see Scourge standing over him, a smirk on the green hedgehog's face as he waved an invitation in the air. Tails' fake smiled, something he learned to do a while back.

"We have a date with some speed tonight." The young ones' ears shot up as he raised a questioning eyebrow. Scourge blinked a few times.

"What?"

"Speed?"

"Well yeah. You do know what speed is don't cha'?" Tails' only slowly shook his head no, blue eyes bright with bewilderment. The Sonic look alike pinched his temples.

"Crank." He looked at the fox who had the same look on his face. He decided to use a different name."Glass?," he said irritably. Still no dice. He growled, throwing his hands in exasperation as he yelled "Crystal Meth! Chaos, what the hell kid? You're a super genius, you're supposed to know this shit!"

"He's just a kid! Do you really think he knows about this kind of stuff?" Teeth bared, Scourge turned around, ice blue eyes flaring as he stared at the red fox before him. He pointed a finger at her.

"Stay out of this Fox. No one asked for your opinion!"

"You didn't have to," she quickly replied. Before Tails had realized what had happened, he was face to face with the image of Fiona laying on the floor with a red mark on her cheek, her nose bleeding and an angered Scourge starting to storm away. Before he exited the room, he glared at the orange kitsune and told him 'You better be ready by the time I get back or I'll do the same thing to you.' When he heard the door slam and the motorcycle engine pull out of the driveway and rip down the street, Tails rushed over to the red fox and sat her up starting to examine her muzzle.

"Fi! Are you alright?"

"Just fine. Don't worry about me."

"But you're hurt" he replied as he watched her stumble on her feet. She leaned over a bit and started coughing out blood to the young one's horror, the crimson liquid trickling onto the mahogany hardwood floors. Fiona sighed shakily as she looked up to meet the gaze of the fox in front of her and gave him a small smile.

"I'll be fine kid. You should get goin' before Scourge comes back." Before Fiona could try to settle on the couch, she felt Tails start to tug on her arm, his grip tight as he started to lead her towards the door. Confused, she stopped in her place and raised a questioning eyebrow. "What are you doing?"

"Come on. I'm taking you with me" he replied as he started to lead her to the door again. He opened the door to find it raining hard, the rain drops making loud pats as it made contact with the almost black pavement. He took off his jacket and put it around the shoulders of the red fox next to him before leading her outside and slamming the door behind him. Fiona kept looking back at the fox, trying to stop him from leaving but it was no use. Every time she tried, he would only nudge her forward. By the time she had got him to stop, they were at the park a couple miles away from the house. The orange fox was drenched in cold rain water, bangs completely covering one of his eyes as he stared at Fiona with darkened baby blues.

"This isn't a good idea."

"I can't stay there anymore. I can't watch you get beat up constantly and continue doing everything he says. There's no way I'm going to do drugs just to please him!"

"Please Tails. Running away isn't the answer-"

"Are you so sure? It's seemed to work with you guys in the past'" he snapped. His eyes widened a bit as he regretted saying that. Fiona wore a look of shock on her face for a few moments which soon turned to a look of anger and disgust as she tore off Tails' jacket, threw it to the ground and started running away.

"Fiona! Wait!" Before Tails could chase her down, he was knocked to the ground from behind. He grunted as his face made contact with the concrete. He lifted his head up a bit to see blood etched onto the concrete. In the puddle, he could only make out a silhouette, the beads of rain sliding down it's jacket. He bent down and grabbed Tails ankles, starting to drag him down the sidewalk from where he came. Fiona could only watch in horror as the unconscious fox disappeared from sight. It was then she knew what she had to do. She turned around and started to sprint down the empty streets, horrible thoughts coursing through her head as she started to approach the bustling city of Metropolis.

"I have to find Sonic."

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**So yeah. Tails got himself into trouble. Again. But this time it's all on Fiona to get help before it's too late. **

**Yeah. Anyways R&R, stay tuned and hope you enjoyed the chapter**


	8. Chapter 8

_**Here's a nice update for my fellow 'Tails takes Cool Lessons' followers! **_

_**Stay tuned for a story update at the end!~**_

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Knuckles and Sonic were lounging around, watching Sonic boast about his achievements to a very enthusiastic Amy. The white bat rolled her eyes and looked at her hot-headed friend, a look of boredom and lack of interest etched into his rough face. The yawned in exaggeration, one eye partly opened as she looked over at the two hedgehogs across the room. "You'd think Sonic would show just a bit of modesty." The red echidna gave Rouge a once over before deciding that she wasn't a threat to his emerald and sighed.

"I've known that hog for years. I don't think he has an ounce of 'modesty' in his body. Just when you think you've seen it all." He kicked his feet up on the table and put his hands behind his head, letting out another sigh. The bat looked at Knuckles curiously and gave him a seductive smile, trailing one of her fingers lightly along his chest. The echidna shivered, the heat rising to his muzzle as he peered over and into Rouge's aquamarine eyes. In a silky voice, she purred "and I bet a big, strong man like you would have more modesty. Right?" Enticingly she trailed her fingers along his neck until she reached his muzzle. At this point, the echidna was as red as his fur and unsure of what to do. The bat giggled coquettishly and drew herself closer.

"Come on Knuckie-"

Before she could say another word all attention was drawn to the opened door. The door hit the wall with a loud bam, the shadow of an all too familiar fox in sight. Rouge scowled as she stood up from the couch, hands on her hips as her heels tap-tapped the wooden floors. She stopped only a few feet away, eyes staring daggers into the red fox's eyes. Fiona was panting heavily from the run, drenched in rain. Even her socks had been soaked through her knee length boots. The fox's tongue hung out of her mouth, undulating with every breath she took. Fiona reached out to touch Rouge's shoulder but the bat quickly pulled away, the deep hatred still burning holes into her soul. "Get out Fox."

"N-no!" Fiona stumbled forwards, hands on her knees as she stared down at the ground in shame. She sniffled a bit, her nose itchy and runny from her little walk. "P-please. It's about T-Tails..."

Now being settled in the cozy room in front of the fireplace, the fox was able to relax for just a while and calm herself. She had been stripped of her clothing, Amy having offered her robe to keep her warm; and covered. Rouge under Amy's order had given Fiona a nice cup of hot chocolate, with mini marshmallows- also the pink hedgehogettes' order. On either side stood Knuckles and Sonic, Rouge sitting by the window on the recliner for she did not trust the fox. Amy nudged the echidna over and he scooted over and made a spot between him and Fiona. With a nod Amy sat, putting a comforting hand on Fiona's shoulder. The pink hedgehogettes' green eyes screamed for answers but she knew if she wanted them, she would have to be patient and talk them out of the fox. Amy smiled softly at Fiona's innocent glance of curiosity. Fiona hmphed and sipped her cocoa, her mask instantly covering her emotions.

The room was silent with the exception of the rains' pitter-patter and the crackling of the fire. As the agonizing silence went on, the white bat found herself starting to crack. Her nails started digging into the recliners' cushion in frustration, teeth starting to bare. Before she got the chance to rip Fiona's head off, she was cut off by the familiar voice of the blue blur. When she looked at him, her expression softened to one of wonder at the blue's appearance. Now looking at him, she started noticing the dark circles under his eyes, the dead look in his olive green orbs, the paleness of his muzzle- even his physique was thinner than usual. Obvious signs of sleep and eating deprivation.

What caught her attention the most was his voice. His usual cocky and chipper voice had toned down a few notches, shaky and quiet compared to his usual approach in speech. The truth was the legendary speed demon was scared. Scared of what his friend was becoming. Scared of what has happened- what will happen next. Scared of losing him to his anti-self. "Please Fiona. Tails is one of the closest people to family I have left. If I lose him, I'll never live myself down... I mean, he looks up to me. I'm his brother... and I let him down..."

"Sonic..." The bat was utterly speechless. Not once had she ever seen Sonic so sad. So desperate for answers. With a silent sigh she made her way over to the blue ones side, even if that meant being any closer to the fox she despised so greatly, and gently rested her hand on his shoulder, the other hand soothingly running its fingers through his azure quills. The hedgehog bowed his head with a sigh, propping his hands on his knees tightly. Another silence passed among the group, this time because they didn't know what to say. Fiona's blue eyes peered up from her mug, a tinge of darkness being her only sign of pity. She kneeled forward and set the half-empty mug on the coffee table, staying in that position even when she knew she could of just laid back. She knew the situation shouldn't intimidate her- the situation didn't even concern her. But at the same time, she felt she owed Tails a debt. This was not only a chance to repay him- this was her chance to redeem herself.

"Okay... I'll tell you everything I know." Quickly she added "But this doesn't mean I'm going back to you guys so don't get too excited."

Rouge finally seeing her chance gave her a little smirk, arms crossed impatiently. "We don't have all year princess."

Fiona gave the bat a glare but sighed, leaning back in her seat until her head sank back into the couch. She closed her eyes, searching for only the needed bits of information she needed to leak out. The red fox opened her mouth a couple of times to start but nothing would come out, her mouth closing again when she would second guess herself. Finally she spoke. "So you know how Scourge has been influencing Tails-"

"Get on with it," Rouge cut in.

"Anyways" Fiona continued as she ignored Rouge's remark, "Scourge was trying to get your friend to try some drugs. Tails refused but he didn't take it well. He knocked the poor guy out and started dragging him away." Before anyone else could cut in, she continued. "I knew I couldn't take Scourge on myself and decided... that I would come to you guys for help."

This time Knuckles remarked. "And why should we help you?"

Fiona remained silent, once again trying to pick out the right words. She looked at everyone's face individually, stopping at her own as she stared at the window. "You're not helping me! It's Tails. He needs his friends..." She let her sentence trail off, looking at Sonic meaningfully as she said the rest of her sentence. "He needs you Sonic. I know he's been a jerk lately... but he's still the same Tails you grew up with. He's still your little brother... and if you really loved him like your family, you would stand by him no matter what."

The two locked eyes.

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**Aaaand cliffhanger!**

**I know, I keep doing this to you guys. I know you hate it. I know you wanna know what happens. But what's the fun in waiting without a good cliff hanger? :D**

**So, uh, let me explain myself. I haven't updated in a long while... well, I haven't had wifi to update so I haven't been very busy. i still don't have full access but I am able to post this at the moment. There are two more chapters so please be patient. I promise it will be worth it.**

**Til' next time!**

**~Masochist Wolfe**


	9. UPDATE

I know I'm not supposed to do this, but... Oh well. Screw the rules.

I know it's been a very long time since I've last updated this, but I have had some... bumps in the road. Up until recently I bought a new computer. My last computer- which had the last chapters of this story- actually broke. Since it costs more to repair, I just got a new one for my birthday. Unfortunately my files could not be saved so the last chapters to Tails Takes Cool Lessons died with it. As did my spirit. *dramatic pause* ...

Anyways... I just wanted to to ask for everyone's opinion (for whoever still reads this), and I only need one review as an answer.

Should I rewrite the last two chapters? Or should I let this story die?


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